The Reaction of a 10-Methylacridinium Salt with Tertiary Amines

Article abstract of DOI:10.1246/bcsj.65.55

The reaction of 10-methylacridinium perchlorate with a variety of N,N-disubstituted alkylamines or aralkylamines was investigated in the presence or absence of air.In all cases studied, 10-methyl-9,10-dihydroacridine was produced in approximately 50percent yield or more.In addition, either 10-methyl-9(10H)-acridinone or 9-(dialkylamino)-10-methylacridinium perchlorate or both were isolated, each yield being greatly dependent on the bulkiness of alkyl groups on the amines.In the blanket of air, significant amounts of aldehyde was detected.The mechanism was discussed.